KR102344799B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electric device comprising a compound represented by Formula 1, a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the organic electric device do. By including the compound represented by Chemical Formula 1 in the organic material layer, the driving voltage of the organic electric device can be lowered, and luminous efficiency and lifespan can be improved.

Description

A compound for an organic electric device, an organic electric device using the same, and an electronic device thereof

The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

A material used as an organic layer in an organic electric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function. In addition, the light emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the light emission mechanism. have. In addition, the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color according to the emission color.

On the other hand, when only one material is used as a light emitting material, the maximum emission wavelength shifts to a longer wavelength due to intermolecular interaction, and there is a problem in that the color purity is lowered or the efficiency of the device is decreased due to the emission attenuation effect. A host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through the The principle is that when a small amount of a dopant having a smaller energy band gap than that of the host forming the emission layer is mixed in the emission layer, excitons generated in the emission layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is a large-area display, and the size thereof is increasing, so that power consumption greater than the power consumption required for the existing portable display is required. Therefore, power consumption has become a very important factor for a portable display having a limited power supply such as a battery, and the problem of efficiency and lifespan must also be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan. However, the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T ₁ value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifespan and high efficiency can be achieved at the same time. .

Therefore, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer. In other words, in order to sufficiently exhibit the excellent characteristics of an organic electric device, the material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. However, development of a stable and efficient organic material layer material for an organic electric device has not yet been sufficiently developed, and in particular, development of a host material for the light emitting layer is urgently required.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by the following formula.

In another aspect, the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.

By using the compound according to the embodiment of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan of the device can be greatly improved.

1 is an exemplary view of an organic electroluminescent device according to the present invention.

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto. In the present invention, the aryl group or the arylene group includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like. In addition, unless otherwise specified in the present specification, the aryl group includes a fluorenyl group and the arylene group includes a fluorenylene group.

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structures, respectively, unless otherwise specified, " A substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to It includes the case of forming a compound as a spy together.

As used herein, the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like.

As used herein, the term "heterocyclic group" refers to a ring containing heteroatoms such as N, O, S, P or Si instead of carbon forming the ring, and "heteroaryl group" or "heteroarylene group" It includes not only an aromatic ring, but also a non-aromatic ring, such as SO ₂ , P=O, etc. instead of carbon forming a ring, such as the following compound, a compound including a heteroatom group may also be included.

The term "aliphatic ring group" used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.

In the present specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl', and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'. Similarly, in the case of pyrimidine, regardless of the valence, it can be described as 'pyrimidine' or as the 'name of the group' of the valence, such as a pyrimidinyl group in the case of monovalent, pyrimidinylene in the case of divalent. have.

In addition, in the present specification, in describing the compound name or the substituent name, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, and 9,9-dimethylfluorene to die It can be described as methylfluorene. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless there is an explicit explanation, the formula used in the present invention applies the same as the definition of the substituent by the exponential definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring. It can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same as or different from each other.

Hereinafter, the laminated structure of the organic electric device containing the compound of the present invention will be described with reference to FIG. 1 .

In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

Further, when a component, such as a layer, membrane, region, plate, etc., is said to be “on” or “on” another component, this means not only when it is “directly above” another component, but also when another component is in between. It should be understood that cases may be included. Conversely, when it is said that an element is "on top of" another part, it should be understood to mean that there is no other part in the middle.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1 , an organic electric device 100 according to an embodiment of the present invention includes a first electrode 120 , a second electrode 180 , and a first electrode 120 formed on a substrate 110 , and An organic material layer including the compound according to the present invention is included between the second electrodes 180 . In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , an electron injection layer 170 , etc. sequentially stacked on the first electrode 120 . . At this time, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc., and the electron transport layer 160, etc. It may also serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer. The light efficiency improving layer may be formed on a surface of both surfaces of the first electrode that does not contact the organic material layer or on a surface of both surfaces of the second electrode that does not contact the organic material layer.

The compound according to an embodiment of the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170), a host or dopant of the emission layer 150, or a material of the light efficiency improving layer. Preferably, the compound according to Formula 1 of the present invention may be used as a host of the light emitting layer.

On the other hand, even with the same and similar core, the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, so the selection of the core and the combination of sub-substituents coupled thereto In particular, when the energy level and T ₁ value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.

Therefore, in the present invention, by using the compound represented by Formula 1 as a host for the light emitting layer, the energy level and T ₁ value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of the material are optimized, and the lifespan of the organic electric device and efficiency can be improved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 120, and the hole injection layer 130 thereon. , after forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon. have. In addition, an auxiliary light emitting layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150 , and an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160 .

In addition, the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

The organic electric device according to an embodiment of the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on a material used.

In addition, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.

Hereinafter, the compound according to one aspect of the present invention will be described.

The compound according to one aspect of the present invention is represented by the following formula (1).

<Formula 1>

In Formula 1, each symbol may be defined as follows.

X ¹ and X ² are each independently a single bond, S or O, ^{except when both X 1} and X ² are single bonds.

R ¹ to R ¹⁰ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one hetero atom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ) may be selected from the group consisting of, and adjacent groups may be bonded to each other to form a ring. A ring formed by bonding adjacent groups to each other is a C ₆ ~ C ₆₀ aromatic hydrocarbon O, N, S, Si and P containing at least one hetero atom of a C ₂ ~ C ₆₀ heterocycle or C ₃ ~ C ₆₀ may be an aliphatic ring of For example, adjacent R ⁷ and R ⁸ , adjacent R ⁸ and R ^{9 ,} or adjacent R ⁹ and R ¹⁰ may be bonded to each other to form an aromatic ring such as benzene or naphthalene.

When R ¹ to R ¹⁰ are an aryl group, it may be preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group, for example, phenyl, biphenyl, terphenyl, naphthalene, or the like.

When R ^{1 To} R ¹⁰ is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₂ heterocyclic group, such as pyridine, pyrimidine, triazine, quinazoline, quinoline, quinoxaline, dibenzofuran, dibenzothiophene, or the like.

L ¹ is a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one hetero ring C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic cyclic group.

When L ¹ is an arylene group, it may be preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₁₈ arylene group, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc. .

When L ¹ is a heterocyclic group, preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₂ heterocyclic group, such as pyridine, pyrimidine, triazine, pyrazine, quinazoline, quinoline , quinoxaline, benzoquinazoline, benzofuropyrimidine, pyridopyrimidine, benzoquinoxaline, benzothienopyrimidine, benzothienothienopyrimidine, and the like.

Ar ¹ is a C ₆ ~ C ₆₀ aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic cyclic group.

When Ar ¹ is an aryl group, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, 9,9 - It may be dimethyl fluorene or the like.

When Ar ¹ is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₈ heterocyclic group, such as pyridine, pyrimidine, triazine, pyrazine, quinazoline, quinoline , quinoxaline, benzoquinazoline, benzofuropyrimidine, pyridopyrimidine, benzoquinoxaline, benzothienopyrimidine, benzothienothienopyrimidine, carbazole, phenylcarbazole, dibenzofuran , dibenzothiophene, and the like.

The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,

The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

The R ¹ to R ¹⁰ , L ¹ , Ar ¹ , L′, R _a and R _b are each deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ An aliphatic group; C ₇ -C ₂₀ Arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; and -L ² -N(R ^a )(R ^b ) may be further substituted with one or more substituents selected from the group consisting of. Wherein L ² may be defined the same as L ', R ^a and R ^b may be the same definition as the R _a and R _b defined above.

Preferably, Chemical Formula 1 may be represented by one of Chemical Formulas 2 to 5 below.

<Formula 2> <Formula 3>

<Formula 4> <Formula 5>

In the above formula, R ¹ -R ¹⁰ , Ar ¹ and L ¹ are as defined in Formula 1.

Preferably, Chemical Formula 1 may be represented by one of Chemical Formulas 6 to 17 below.

<Formula 6> <Formula 7> <Formula 8>

<Formula 9> <Formula 10> <Formula 11>

<Formula 12> <Formula 13> <Formula 14>

<Formula 15> <Formula 16> <Formula 17>

In the above formula, R ¹¹ to R ¹⁴ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one hetero atom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; and -L ² -N(R ^a )(R ^b ), and adjacent groups may be bonded to each other to form a ring. A ring formed by bonding adjacent groups to each other is a C ₆ ~ C ₆₀ aromatic hydrocarbon O, N, S, Si and P containing at least one hetero atom of a C ₂ ~ C ₆₀ heterocycle or C ₃ ~ C ₆₀ may be an aliphatic ring of

R ¹ -R ¹⁰ , Ar ¹ , L ¹ are as defined in Formula 1, L ² may be defined as L' defined in Formula 1, R ^a , R ^b are R defined in Formula 1 _a , may be defined the same as _{R b .}

Preferably, R ¹¹ to R ¹⁴ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₂₀ Aryl group; O, N, S, Si and P containing at least one hetero atom C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₂₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; and -L ² -N(R ^a )(R ^b ).

Specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.

.

.

In another aspect, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is one type represented by Formula 1 A single compound or two or more types of compounds are included.

The organic layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and preferably, the compound is included in the light emitting layer.

Synthesis example

The compound represented by Formula 1 according to the present invention may be synthesized by reacting Sub-1 and Sub-2 as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

I. Synthesis of Sub-1

Sub-1 of Scheme 1 may be synthesized by the following reaction route, but is not limited thereto.

(1) Sub-1-1 synthesis

Synthesis of Sub-1-1-a

2-chloroacenaphthylene-1-carbaldehyde (9.20 g, 42.86 mmol), methyl thioglycollate (27.28 g, 68.58 mmol), and triethylamine (8.33 ml, 82.29 mmol) are added to pyridine (200 ml) and stirred at 0°C for 45 minutes. . Thereafter, after raising the temperature to 60° C. and stirring for 30 minutes, KOH (20 ml, 48%) aqueous solution was added at room temperature and stirred for 10 minutes. After extraction with MC, wiping with water, and concentration to remove the solvent, 10.16 g (89 %) of the product was obtained.

Synthesis of Sub-1-1-b

KOH (5.46 g, 97.26 mmol), ethanol (400 ml), and H ₂ O (200 ml) were added to Sub-1-1-a (7.40 g, 27.79 mmol) and refluxed at 80° C. for 5 hours. When the reaction is complete, it is concentrated to remove ethanol, diluted in water, and acidified by adding 6N HCl. The resulting solid was filtered, washed with water, and dried to obtain 6.73 g (96%) of the product.

Synthesis of Sub-1-1-c

Copper chromite (0.26 g, 0.82 mmol) and quinoline (120 ml) were added to Sub-1-1-b (4.20 g, 16.45 mmol) and refluxed at 240° C. for 8 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and filtered. The filtered material was acid-treated with HCl at 0° C., extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by a silica gel column to obtain 3.32 g (97%) of the product.

Synthesis of Sub-1--1-d

After MC (50 mL) was added to Sub-1-1-c (3.80 g, 18.24 mmol), N- bromosuccinimide (3.25 mL, 18.24 mmol) was slowly added, followed by stirring at room temperature for 6 hours. When the reaction is complete, extract with MC and wash with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by a silica gel column to obtain 4.61 g (88%) of a product.

Synthesis of Sub-1-1-e

Sub-1-1-d (5.10 g, 17.76 mmol) in 2-chloroaniline (2.27 g, 17.76 mmol), Pd ₂ (dba) ₃ (0.33 g, 0.36 mmol), t-BuONa (3.41 g, 35.52 mmol) , P(t-bu) ₃ (0.14 g, 0.71 mmol), and toluene (50 ml) were added and stirred at 70°C. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by a silica gel column to obtain 5.40 g (91%) of a product.

Synthesis of Sub-1-1

Sub-1-1-e (2.90 g, 8.69 mmol) in Pd(OAc) ₂ (0.10 g, 0.43 mmol), P(t-Bu) ₃ (0.25 g, 0.87 mmol), K ₂ CO ₃ (3.60 g) , 26.06 mmol) and DMA (50 ml) were added and refluxed at 170° C. for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by a silica gel column to obtain 2.17 g (84%) of a product.

(2) Sub-1-2 synthesis

Synthesis of Sub-1--2-a

Sub-1-d (2.70 g, 9.40 mmol), 2-chloronaphthalen-1-amine (1.67 g, 9.40 mmol), Pd ₂ (dba) ₃ (0.17 g, 0.19 mmol), t-BuONa (1.81 g) , 18.80 mmol), P(t-bu) ₃ (0.08 g, 0.38 mmol), and toluene (50 ml) were reacted in the same manner as in the synthesis method of Sub-1-1-e above, and 3.21 g (89%) of the product ) was obtained.

Synthesis of Sub-1-2

Sub-1-2-a (5.90 g, 15.37 mmol), Pd(OAc) ₂ (0.17 g, 0.77 mmol), P(t-Bu) ₃ (0.45 g, 1.54 mmol), K ₂ CO ₃ (6.37 g) , 46.11 mmol) and DMA (80 ml) were reacted to obtain 4.22 g (79%) of the product in the same manner as in the synthesis of Sub-1-1.

(3) Sub-1-3 synthesis

Synthesis of Sub-1-3-a

Sub-1-1-d (1.90 g, 6.62 mmol), 3-chloronaphthalen-2-amine (1.18 g, 6.62 mmol), Pd ₂ (dba) ₃ (0.18 g, 0.20 mmol), t-BuONa (1.27 g) , 13.23 mmol), P(t-bu) ₃ (0.08 g, 0.40 mmol), and toluene (40 ml) were reacted in the same manner as in the synthesis method of Sub-1-1-e above, and 2.18 g (86%) of the product ) was obtained.

Synthesis of Sub-1-3

Sub-1-3-a (1.20 g, 3.13 mmol), Pd(OAc) ₂ (0.04 g, 0.16 mmol), P(t-Bu) ₃ (0.09 g, 0.31 mmol), K ₂ CO ₃ (1.30 g) , 9.38 mmol) and DMA (30 ml) were reacted in the same manner as in the synthesis method of Sub-1-1 to obtain 0.88 g (81%) of the product.

(4) Sub-1-4 synthesis

Synthesis of Sub-1-4-a

Sub-1-1-d (2.50 g, 8.71 mmol), 1-chloronaphthalen-2-amine (1.55 g, 8.71 mmol), Pd ₂ (dba) ₃ (0.24 g, 0.26 mmol), t-BuONa (1.67 g) , 17.41 mmol), P(t-bu) ₃ (0.11 g, 0.52 mmol), and toluene (40 ml) were reacted in the same manner as in the synthesis method of Sub-1-1-e, and 2.91 g (87%) of the product ) was obtained.

Synthesis of Sub-1-4

Sub-1-4-a (3.10 g, 8.08 mmol), Pd(OAc) ₂ (0.09 g, 0.40 mmol), P(t-Bu) ₃ (0.23 g, 0.81 mmol), K ₂ CO ₃ (3.35 g) , 24.23 mmol) and DMA (50 ml) were reacted in the same manner as in the synthesis of Sub-1-1 to obtain 2.30 g (82%) of the product.

(5) Sub-1-5 synthesis

Synthesis of Sub-1-5-a

Sub-1-1-d (6.70 g, 23.33 mmol), 4-chloro-[1,1'-biphenyl]-3-amine (4.75 g, 23.33 mmol), Pd ₂ (dba) ₃ (0.64 g, 0.70) mmol), t-BuONa (4.48 g, 46.66 mmol), P(t-bu) ₃ (0.28 g, 1.40 mmol), and toluene (90 ml) were reacted in the same manner as in the synthesis method of Sub-1-1-e. was carried out to obtain 8.61 g (90%) of the product.

Synthesis of Sub-1-5

Sub-1-5-a (5.90 g, 14.39 mmol), Pd(OAc) ₂ (0.16 g, 0.72 mmol), P(t-Bu) ₃ (0.42 g, 1.44 mmol), K ₂ CO ₃ (5.97 g) , 43.18 mmol) and DMA (80 ml) were reacted in the same manner as in the synthesis of Sub-1-1 to obtain 4.73 g (88%) of the product.

(6) Sub-1-6 synthesis

Synthesis of Sub-1-6-a

Sub-1-1-d (8.70 g, 30.30 mmol) in (2-nitrophenyl)boronic acid (5.06 g, 30.30 mmol), Pd ₂ (dba) ₃ (0.83 g, 0.91 mmol), NaOH (3.64 g, 90.89) mmol), P(t-Bu) ₃ (0.37 g, 1.82 mmol), THF (100 ml), and H ₂ O (50 ml) were added and refluxed at 90° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by a silica gel column to obtain 9.08 g (91%) of the product.

Synthesis of Sub-1-6

Add triphenylphosphine (15.73 g, 59.96 mmol) and o-dichlorobenzene (o-DCB) (100 ml) to Sub-1-6-a (7.90 g, 23.99 mmol) and reflux at 180° C. for 6 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, and o-DCB is removed. Thereafter, the mixture was separated by a silica gel column to obtain 6.13 g (86%) of the product.

(7) Sub-1-7 synthesis

Synthesis of Sub-1-7-a

Sub-1-1-d (3.30 g, 11.49 mmol), (1-nitronaphthalen-2-yl)boronic acid (2.49 g, 11.49 mmol), Pd ₂ (dba) ₃ (0.32 g, 0.34 mmol), NaOH ( 1.38 g, 34.47 mmol), P(t-Bu) ₃ (0.14 g, 0.69 mmol), THF (80 ml), and H ₂ O (40 ml) were prepared in the same manner as in the synthesis method of Sub-1-6-a above. The reaction proceeded to obtain 3.18 g (84%) of the product.

Synthesis of Sub-1-7

Sub-1-7-a (1.33 g, 3.51 mmol), triphenylphosphine (2.30 g, 8.76 mmol), and o-dichlorobenzene (o-DCB) (10 ml) were reacted in the same manner as in the synthesis method of Sub-1-6 above. was carried out to obtain 1.08 g (89%) of the product.

(8) Sub-1-8 synthesis

Synthesis of Sub-1-8-a

Sub-1-1-d (6.40 g, 22.29 mmol), (3-nitronaphthalen-2-yl)boronic acid (4.84 g, 22.29 mmol), Pd ₂ (dba) ₃ (0.61 g, 0.67 mmol), NaOH ( 2.67 g, 66.86 mmol), P(t-Bu) ₃ (0.27 g, 1.34 mmol), THF (80 ml), and H ₂ O (40 ml) were prepared in the same manner as in Sub-1-6-a above. The reaction proceeded to obtain 6.39 g (87%) of the product.

Synthesis of Sub-1-8

Sub-1-8-a (5.80 g, 15.29 mmol), triphenylphosphine (10.02 g, 38.22 mmol), and o-dichlorobenzene (o-DCB) (100 ml) were reacted in the same manner as in the synthesis method of Sub-1-6 above. was carried out to obtain 4.41 g (83%) of the product.

(9) Sub-1-9 synthesis

Synthesis of Sub-1-9-a

Sub-1-1-d (8.10 g, 28.21 mmol), (2-nitronaphthalen-1-yl)boronic acid (6.12 g, 28.21 mmol), Pd ₂ (dba) ₃ (0.77 g, 0.85 mmol), NaOH ( 3.38 g, 84.62 mmol), P(t-Bu) ₃ (0.34 g, 1.69 mmol), THF (100 ml), and H ₂ O (50 ml) were prepared in the same manner as in the synthesis method of Sub-1-6-a above. The reaction proceeded to obtain 7.71 g (83%) of the product.

Synthesis of Sub-1-9

Sub-1-9-a (6.90 g, 18.19 mmol), triphenylphosphine (11.92 g, 45.46 mmol), and o-dichlorobenzene (o-DCB) (100 ml) were reacted in the same manner as in the synthesis method of Sub-1-6 above. was carried out to obtain 5.37 g (85%) of the product.

(10) Sub-1-10 synthesis

Synthesis of Sub-1-10-a

Sub-1-1-d (2.80 g, 9.75 mmol), (4-nitro-[1,1'-biphenyl]-3-yl)boronic acid (2.37 g, 9.75 mmol), Pd ₂ (dba) ₃ ( 0.27 g, 0.29 mmol), NaOH (1.17 g, 29.25 mmol), P(t-Bu) ₃ (0.12 g, 0.59 mmol), THF (100 ml), H ₂ O (50 ml) above Sub-1- The reaction was carried out in the same manner as in the synthesis method of 6-a to obtain 3.56 g (90%) of the product.

Synthesis of Sub-1-10

Sub-1-10-a (1.90 g, 4.69 mmol), triphenylphosphine (4.38 g, 11.71 mmol), and o-dichlorobenzene (o-DCB) (10 ml) were reacted in the same manner as in the synthesis method of Sub-1-6 above. was carried out to obtain 1.32 g (81%) of the product.

(11) Sub-1-19 synthesis

Synthesis of Sub-1-19-a

2-chloroacenaphthylene-1-carbaldehyde (3.90 g, 18.17 mmol), methyl glycolate (2.46 g, 27.25 mmol) and pyridine (50 ml) were added with triethylamine (2.73 g, 34.52 mmol) and stirred at 0 °C for 45 minutes. Thereafter, after stirring at 60° C. for 30 minutes, an aqueous solution of KOH (10 ml, 48%) was added at room temperature and stirred for 10 minutes. After extraction with MC and wiping with water, the solvent was concentrated to obtain 2.77 g (61%) of the product.

Synthesis of Sub-1-19-b

Sub-1-19-a (4.90 g, 19.58 mmol), KOH (3.85 g, 68.53 mmol), ethanol (300 ml), and H ₂ O (150 ml) were added in the same manner as in the synthesis method of Sub-1-1-b above. The reaction proceeded in this way to obtain 4.35 g (94%) of the product.

Synthesis of Sub-1-19-c

Sub-1-19-b (3.10 g, 13.12 mmol), copper chromite (0.11 g, 0.66 mmol), and quinoline (60 ml) were reacted in the same manner as in the synthesis method of Sub-1-1-c, and the product was 2.40 g (95%) were obtained.

Synthesis of Sub-1-19-d

Sub-1-19-c (5.1 g, 26.53 mmol), N- bromosuccinimide (4.72 mL, 26.53 mmol), and MC (80 mL) were reacted in the same manner as in the synthesis method of Sub-1-1-d. 6.47 g (90%) of product were obtained.

Synthesis of Sub-1-19-e

Sub-1-19-d (2.20 g, 8.11 mmol), 2-chloroaniline (1.04 g, 8.11 mmol), Pd ₂ (dba) ₃ (0.15 g, 0.16 mmol), t-BuONa (1.56 g, 16.23 mmol) , P(t-bu) ₃ (0.07 g, 0.32 mmol), and toluene (50 ml) were reacted in the same manner as in the synthesis method of Sub-1-1-e to obtain 2.09 g (81%) of the product.

Synthesis of Sub-1-19

Sub-1-19-e (4.10 g, 12.90 mmol), Pd(OAc) ₂ (0.15 g, 0.65 mmol), P(t-Bu) ₃ (0.37 g, 1.29 mmol), K ₂ CO ₃ (5.35 g) , 38.71 mmol) and DMA (80 ml) were reacted in the same manner as in the synthesis of Sub-1-1 to obtain 2.76 g (76%) of the product.

(12) Sub-1-23 synthesis

Synthesis of Sub-1-23-a

Sub-1-19-d (5.90 g, 21.76 mmol), (2-nitrophenyl)boronic acid (3.63 g, 21.76 mmol), Pd ₂ (dba) ₃ (0.60 g, 0.65 mmol), NaOH (2.61 g, 65.29) mmol), P(t-Bu) ₃ (0.53 g, 1.31 mmol), THF (100 ml), and H ₂ O (50 ml) were reacted in the same manner as in the synthesis method of Sub-1-6-a, 5.86 g (86%) of the product were obtained.

Synthesis of Sub-1-23

Sub-1-23-a (2.80 g, 8.94 mmol), triphenylphosphine (6.29 g, 22.34 mmol), and o-DCB (100 ml) were reacted in the same manner as in the synthesis method of Sub-1-6 above to produce 2.04 g (81%) was obtained.

The compound belonging to Sub-1 may be the following compounds, but is not limited thereto, and Table 1 shows FD-MS values of the compounds belonging to Sub-1.

[Table 1]

II. Sub-2 example

The compound belonging to Sub-2 of Scheme 1 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS values of the following compounds.

[Table 2]

Ⅲ. Synthesis of final compound

(1) Synthesis of P-14

Sub-1-1 (2.10 g, 7.06 mmol) to Sub-2-1 (1.89 g, 7.06 mmol), Pd ₂ (dba) ₃ (0.19 g, 0.21 mmol), t-BuONa (1.36 g, 14.12 mmol) , P(t-bu) ₃ (0.09 g, 0.42 mmol), and toluene (40ml) were added and refluxed at 120° C. for 3 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. Thereafter, the organic layer _{was dried over MgSO 4} , concentrated, and separated using a silica gel column filter to obtain 3.10 g (83%) of a product.

(2) Synthesis of P-18

Sub-1-5 (1.80 g, 4.82 mmol), Sub-2-49 (1.51 g, 4.82 mmol), Pd ₂ (dba) ₃ (0.13 g, 0.14 mmol), t-BuONa (0.93 g, 9.64 mmol) , P(t-bu) ₃ (0.06 g, 0.29 mmol), and toluene (40 ml) were reacted in the same manner as in the synthesis of P-14 to obtain 2.87 g (91%) of the product.

(3) Synthesis of P-32

Sub-1-2 (3.30 g, 9.50 mmol), Sub-2-26 (3.14 g, 9.50 mmol), Pd ₂ (dba) ₃ (0.26 g, 0.28 mmol), t-BuONa (1.83 g, 19.00 mmol) , P(t-bu) ₃ (0.12 g, 0.57 mmol), and toluene (50 ml) were reacted in the same manner as in the synthesis of P-14 to obtain 4.32 g (86%) of the product.

(4) Synthesis of P-43

Sub-1-6 (2.30 g, 7.73 mmol), Sub-2-41 (2.25 g, 7.73 mmol), Pd ₂ (dba) ₃ (0.14 g, 0.15 mmol), t-BuONa (1.49 g, 15.47 mmol) , P(t-bu) ₃ (0.06 g, 0.31 mmol), and toluene (30 ml) were reacted in the same manner as in the synthesis of P-14 to obtain 3.63 g (85%) of the product.

(5) Synthesis of P-73

Sub-1-8 (5.10 g, 14.68 mmol), Sub-2-50 (3.92 g, 14.68 mmol), Pd ₂ (dba) ₃ (0.27 g, 0.29 mmol), t-BuONa (2.82 g, 29.36 mmol) , P(t-bu) ₃ (0.12 g, 0.59 mmol), and toluene (70 ml) were reacted in the same manner as in the synthesis of P-14 to obtain 6.87 g (81%) of the product.

(6) Synthesis of P-76

Sub-1-9 (2.20 g, 6.33 mmol), Sub-2-58 (1.52 g, 6.33 mmol), Pd ₂ (dba) ₃ (0.12 g, 0.13 mmol), t-BuONa (1.22 g, 12.66 mmol) , P(t-bu) ₃ (0.05 g, 0.25 mmol), and toluene (30 ml) were reacted in the same manner as in the synthesis of P-14 to obtain 1.43 g (41%) of the product.

(7) Synthesis of P-82

Sub-1-19 (3.90 g, 13.86 mmol), Sub-2-44 (4.59 g, 13.86 mmol), Pd ₂ (dba) ₃ (0.25 g, 0.28 mmol), t-BuONa (2.66 g, 27.73 mmol) , P(t-bu) ₃ (0.11 g, 0.55 mmol), and toluene (60 ml) were reacted in the same manner as in the synthesis of P-14 to obtain 7.02 g (88%) of the product.

(8) Synthesis of P-90

Sub-1-23 (3.70 g, 13.15 mmol), Sub-2-50 (3.51 g, 13.15 mmol), Pd ₂ (dba) ₃ (0.24 g, 0.26 mmol), t-BuONa (2.53 g, 26.31 mmol) , P(t-bu) ₃ (0.11 g, 0.53 mmol), and toluene (80 ml) were reacted in the same manner as in the synthesis of P-14 to obtain 5.32 g (79%) of the product.

The FD-MS values of the compounds P-1 to P-95 of the present invention prepared by the same method as the synthesis method are shown in Table 3 below.

[Table 3]

Manufacturing evaluation of organic electric devices

[Example 1] Red Manufacturing and testing of organic light emitting devices

^{N 1} -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene on the ITO layer (anode) formed on the glass substrate After vacuum deposition of a -1,4-diamine film to form a 60 nm-thick hole injection layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl on the hole injection layer was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Then, on the hole transport layer, the compound P-1 of the present invention as a host and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate as a dopant were doped in a 95:5 weight ratio to deposit a light emitting layer to a thickness of 30 nm. Then, 1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer.

Then, Bis(10-hydroxybenzo[h]quinolinato)beryllium was formed to a thickness of 40 nm to form an electron transport layer, and then LiF was deposited to a thickness of 0.2 nm to form an electron injection layer, followed by Al to a thickness of 150 nm. It was deposited as a cathode.

[ Example 2] to [ Example 20]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-1 of the present invention as a host.

[ comparative example 1] to [ comparative example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of Comparative Compounds 1 to 4 was used as a host instead of Compound P-1 of the present invention.

<Comparative compound 1> <Comparative compound 2> <Comparative compound 3> <Comparative compound 4>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 20 and Comparative Examples 1 to 4, the electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, At 2500cd/m ² standard luminance, T95 lifetime was measured using a lifetime measuring device manufactured by McScience, and the measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, the organic light emitting device using the material for an organic light emitting device of the present invention represented by Chemical Formula 1 as a phosphorescent host has significantly improved driving voltage, efficiency and lifespan.

Specifically, when Comparative Compound 2 to Comparative Compound 4 having a 5- or 6-ring heterocyclic core as a core than Comparative Compound 1 (CBP), which is generally used as a host material, is used as a host, the driving voltage is lowered and the efficiency and Lifespan was improved, and when the compound of the present invention in which indole was condensed with acenaphthothiophene or acenaphthofuran was used as a host, driving voltage, efficiency and lifespan were significantly improved.

When the indole is condensed with acenaphthothiophene or acenaphthofuran, the value of the energy level (especially the HOMO level) is different from those of Comparative Compounds 2 to 4, and the charge balance in the light emitting layer is improved by changing the physical properties of the compound. As it increases, light emission is well achieved inside the light emitting layer rather than the interface of the light emitting layer. As a result, deterioration at the interface of the light emitting layer is also reduced, and it is judged that the driving voltage, efficiency, and lifespan are improved. Therefore, it is judged that this point acts as a major factor in improving device performance during device deposition.

The above description is merely illustrative of the present invention, and various modifications will be possible without departing from the essential characteristics of the present invention by those skilled in the art to which the present invention pertains. Accordingly, the embodiments disclosed in the present specification are intended to illustrate rather than limit the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100: organic electric device 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (11)

A compound represented by the following formula (1):
<Formula 1>

In Formula 1,
X ¹ and X ² are each independently a single bond, S or O, ^{except when both X 1} and X ² are single bonds,
R ¹ to R ¹⁰ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one hetero atom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L'-N(R _a ) (R _b ) is selected from the group consisting of, adjacent groups may combine with each other to form a ring,
L ¹ is a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one hetero ring C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ is selected from the group consisting of an aliphatic cyclic group,
Ar ¹ is a C ₆ ~ C ₆₀ aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group. The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 2 to 5:
<Formula 2><Formula3>

<Formula 4><Formula5>

In the above formula, R ¹ -R ¹⁰ , Ar ¹ and L ¹ are as defined in claim 1. The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 6 to 17:
<Formula 6><Formula7><Formula8>

<Formula 9><Formula10><Formula11>

<Formula 12><Formula13><Formula14>

<Formula 15><Formula16><Formula17>

In the above formula, R ¹ -R ¹⁰ , Ar ¹ , L ¹ are as defined in claim 1,
R ¹¹ to R ¹⁴ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one hetero atom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; And -L ² -N(R ^a ) (R ^b ) is selected from the group consisting of, adjacent groups may combine with each other to form a ring,
Wherein L ² is defined in the same manner as in paragraph (1) L ', R ^a, R ^b are defined as in claim 1 R _a, R _b. The method of claim 1,
The compound represented by Formula 1 is a compound, characterized in that one of the following compounds:

. An organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising one single compound or two or more compounds represented by the formula (1) of claim 1. 6. The method of claim 5,
The organic material layer is an organic electric device comprising at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer. 7. The method of claim 6,
The compound is an organic electric device, characterized in that contained in the light emitting layer. 6. The method of claim 5,
The organic material layer is an organic electric device, characterized in that formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. 6. The method of claim 5,
The organic electric device further comprising a light efficiency improving layer formed on a surface of both surfaces of the first electrode or the second electrode that is not in contact with the organic material layer. A display device comprising the organic electric device of claim 5; and
An electronic device comprising a; a control unit for driving the display device. 11. The method of claim 10,
The organic electric device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, an electronic device, characterized in that selected from the group consisting of a single color lighting device and a quantum dot display device.

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